Things the Winchesters Learned the Hard Way
by crazybeagle
Summary: Dean, Sam, and the many life lessons they've learned on the road. Because hey, wisdom can only be gained through adversity, right? Oneshot series. Hilarity will ensue.
1. Chapter 1

_**Things the Winchesters Learned the Hard Way**_

**AN: This will be a series of comedic oneshots, in which we get to spend some quality time with Dean and Sam and see the many lessons they've learned from life on the road. Because hey, we all gotta learn from our screwups, right? And a Winchester screwup generally tends to be far more epic than any normal person's screwup. **

**So, without further ado….**

_**Winchester Life Lesson Number One: Don't try to hit on girls while doing post-hunt laundry. Especially with your brother there.**_

Wintertime hunts were always a huge pain. Obviously, it was cold, and that sucked—really _really_ sucked, especially when it was some Big Ugly that had taken them days to find, whose lair was in the middle of the damn woods in Washington state miles away from any civilization, in _January_, in the _rain_—but what sucked the most?

Doing the laundry afterwards.

As if post-hunt laundry wasn't bad enough—dirt, sweat, gunpowder, oftentimes nasty gunk and body fluids from whatever the hell it was they'd been hunting, and blood.

Yeah, Dean would venture to say that the blood was the worst part.  
Especially when you're at a Laundromat with your idiot little brother.

And trying to hit on a girl.

Now generally, when they were doing particularly nasty post-hunt laundry, they tried to take care of most of the ugly stuff back at the motel—the clothing that was particularly ripped, bloody, or covered with monster goo. Stuff that would raise both eyebrows and questions. Neither of them cared to repeat the Amarillo, Texas incident: back when they were both kids, some schmuck with admittedly good intentions took one glance at Dad's bloody laundry pile and called the cops on them. It had taken a great deal of smooth talking on Dad's part—and the irresistible cuteness of a four-year-old Sam—to keep them from getting arrested. They never made that mistake again, and since then, Dean and Sam had become laundry experts. And it was damn useful, too, because even though replacing your clothes more frequently than you'd like came with being a Hunter, they had a knack for clothing preservation. Not that Dean would ever admit to anybody the fact that he owned a sewing kit for this purpose….

But today just happened to be the one day that they'd been careless about it.

And—_thanks a lot, Sammy_—now this girl was staring at him like he could be an axe murderer.

Or…something else, he thought, noting how grossed out she looked as she gaped between Dean and Sam.

All because of Sam and that one damn pair of bloody boxers…

…Or three.

The Laundromat excursion had begun relatively well, despite the shit-tacular hunt that had ended the night before. The hunt had left them both exhausted, irritable, beat to hell, and pretty cut up, because this particular Big Ugly had had obnoxiously impressive claws and teeth and knew how to use them. So that night at the motel, the laundry was pretty much forgotten. They'd gotten to spend some quality time with stitches, antiseptic, and cheap liquor, with a bad kung fu movie playing in the background as a pathetic attempt to distract themselves. The fact that proper medical treatment was a luxury they couldn't usually afford was a testament to how much their lives could suck sometimes, but hey, could be worse. And at least the kung fu movie was the hilarious kind of bad, and not just _bad_ bad.

At any rate, Dean had woken up today feeling much better and eager to get on the road again. Sam, on the other hand, who'd gotten attacked from behind yesterday and gotten his back slashed up pretty good, was still tired and exceedingly grouchy from a moderate amount of blood loss. But he declined Dean's offer to do both their laundry and let him get some sleep, adamant that he wanted to get the hell out of this town. Dean was with him on that one, so they'd gone together, ready to hit the highway immediately afterward.

Thankfully, it was a backwoods kind of town, because even though the mud masked some of the blood that had made it onto the outfit Dean had worn yesterday—some of it his but a lot of it Sam's—a blissfully uncrowded Laundromat meant that he didn't have to explain away the articles of clothing that looked like they ought to be pieces of evidence in a crime scene investigation. He'd done his best to get the worst of the stains out that morning in the motel, doing what he could with cold water and even a little bottle of the motel's shampoo, but even so he'd had to shove them in the washer quickly before anybody saw. He'd decide once they came out of the wash whether it was worth it to keep them or not.

Other than that, he saw no reason why he shouldn't be able to simultaneously wash the rest of his clothes and hit on the one hot girl who'd showed up to do her own laundry. Because, he figured, a guy doing laundry? Approachable. Hot guy doing laundry? _Very _approachable. Hot guy doing slightly worn-out, drifter-type laundry? Steve freaking McQueen.

And this girl was totally eating it up.

She was a pretty little blonde thing in that magical, unguessable age range between 20 and 25, named Mindy or Mandy—he wasn't sure which—and she probably couldn't guess the first thing about him if she tried. And she seemed to find that sexy. Huh. Must be a small-town-girl thing.

So he played along, giving her purposefully cryptic answers whenever she asked him something about himself, amused that she was so into the whole supposed "aura of mystery" thing.

"So…" Mindy/Mandy had asked, very non-discreetly removing a lacy bra from a dryer and folding it, oh so slowly. "Where are you from…Steve?"

He grinned, eyes on that lacy bra, and shrugged. "Around."

"Really?" she giggled. "Where's _around_?"

He paused, trying to think of something equally ambiguous to tell her, but Mindy/Mandy's attention had drifted to Sam, who was doing his own laundry on the far side of the long room. He was giving Dean a spectacular bitchface, one that clearly said _Stop hitting on girls because I wanna get out of here ASAP and there's no WAY I'm gonna hang out here another night waiting around while you're out getting laid._

"Um…who's your friend?" Mindy/Mandy asked uncertainly.

Dean rolled his eyes. "Eh, don't worry 'bout him. That's just Sammy. My little brother."

"He looks a little…" she trailed off, obviously trying to find a polite word to describe the look that Sam was directing at the two of them.

Dean shrugged. "He's just a little hung over, is all. Wants me to hurry up and finish so we can go and he can grab himself a Bloody Mary."

She blinked. "Oh. Then maybe…I should—"

"Nah, there's no rush," Dean said dismissively. "He can kiss my ass. Besides…" he gave her an appraising look. "I like laundry."

She smiled and blushed a little. "Me too." She tucked a strand of hair behind her ear. "So Steve—"

But she was cut off by an abrupt call of "Hey, Dean!" from the back of the room.

Dean closed his eyes for a fraction of a second. _Dammit, Sam…_

Mindy/Mandy looked back at Sam, and then at Dean, eyes narrowing in confusion. "Um…_Dean_? But I thought your name was…"

Dean had a gift for smooth recoveries. He chuckled and shook his head. "It is. It's Steve. Sammy's the only one who calls me that, really. It's actually my middle name, and the kid watched _Rebel Without a Cause _one too many times growing up, and I guess the name kinda stuck. Stupid, I know, but yeah." He smiled for good measure.

Even so, he wasn't sure she'd buy it, but fortunately, her own face broke out into a smile. "Really?"

"Yeah."

"That's adorable."

Apparently, she was the type to go for endearing guys as well as mysterious.

_Well, whatever works, I guess…_

"Dean," Sam called again, a little more insistently. He looked pissed.

Dean bit back an agitated growl. Whatever it was Sam wanted, Dean knew he wasn't going to stop pestering him until he came, and then Mindy/Mandy time would be as good as over. It was the path of least resistance, really, to just go over and deal with him now.

"Erm, 'scuse me for a minute," he said with an apologetic grin. "Better go make sure he's not about to go put a red shirt in with his tighty whities. Kid probably can't see straight right now."

Mindy/Mandy nodded. "Sure. No problem."

"Dean!"

"I'm coming, I'm coming," he grumbled, putting the laundry basket down on a nearby table and stalking to the back of the store. "I'm a little busy, Sammy," he said in an undertone when he reached his brother, who was loading wet clothes into a dryer. "What do you want?"

"What the hell are you doing?" Sam jerked his head in the direction of Mindy/Mandy, who was not-so-inconspicuously watching them from the front of the store.

"What the hell do you think?" Dean smirked. "Now if you don't mind, I'm a little busy—" He started to walk away, but Sam stepped in front of him.

"Doing what?"

Dean frowned. "Doing laundry. Move." He tried to sidestep him.

"Dude, you haven't even started a load yet. You put in like a shirt and one pair of pants. I've been watching."

"You've been _watching_?" Dean raised an eyebrow. "Well. That's not pervy of you _at all_, is it, Sammy. I for one feel violated."

Sam ignored that. "So you've been busy with _other _stuff, then." He looked over at Mindy/Mandy, still folding her underwear.

"Yup."

"And how's that going for you?"

"Awesome. That is, until you interrupted."

"So what's her name?" Sam crossed his arms.

"Mindy. Or, er, Mandy. I'm not really sure, actually."

"Oh, it's really going _awesome_ then, isn't it," Sam scoffed.

Dean glowered up at him. Didn't matter if the kid was 6'4". He was still a little smartass. "Yes, as a matter of fact it is. Now if you don't mind—"

Sam stepped out of his way. "Fine. Whatever. Just do your laundry, okay? I wanna get out of here."

"I woulda left you at the motel if I'd known you were gonna bitch at me the whole time, Sammy." Come to think of it, he probably really should have left Sam at the motel. He was a still pretty pale and looked like he hadn't slept in a week.

Sam raised his eyebrows. "If you had, you wouldn't have come back for me until dinnertime, at least." With another glance at Mindy/Mandy, he added, "or later."

"Yeah, well. Woulda been time well-spent. Seriously, though," he added, "you look dead on your feet, dude. You sure you're okay?"

He shrugged. "It's just laundry."

"You can sit down, if you want. I can finish these," he said with a nod at Sam's laundry basket.

Sam shook his head, looking amused. "Then we really _will_ be here 'till dinner time. I got it. Just get yours done, okay?"

"Yeah, okay." He started to walk back toward the front but stopped when he heard, barely audible over the _thrum_ of the few running machines—

"Uh…Dean?"

He turned around. "Yeah?"

"Actually, can you, uh, help me out with something real quick?" He glanced around furtively as he said this, as if to make sure none of the other occupants of the Laundromat were looking their way.

"What?"

"Uh, there's some blood on some of my…uh, stuff…that I can't figure out how to get out."

"What _stuff_?" Dean asked suspiciously.

"Well…" Sam rummaged through his bag of dirty clothes, and as discreetly as he could, produced a wad of boxer shorts. There were three of them, and all were soaked through with big, dried blotches of blood.

Dean rolled his eyes. "Oh, God…"  
Sam just frowned at him.

"Those look like _personal_ stains to me," Dean drawled, though he looked up to make sure Mindy/Mandy was looking elsewhere. "You're a big boy now, Sammy. Gotta handle this stuff on your own."

"Dean, come on," Sam growled, though he looked more than a little embarrassed. "We're kinda low on cash right now and we can't really afford to replace this stuff. And besides, some of it's your blood anyway."

Dean snatched the boxers from him. "Geez, Sam, can you not _say_ that so loud?" he said in a harsh whisper. "And what do you mean _my _blood?" he added incredulously.

"Well these are the ones I was wearing yesterday," he said, jabbing a finger at one of the pairs. "The blood from those gashes kinda got everywhere, and I mean _everywhere_. You already know I had to throw the shirt and the jacket away 'cause they were beyond hope. But those other two?" he asked, annoyance leaking into his voice, "If you remember, you grabbed 'em out of my bag yesterday when we got back to the room to mop yourself up with, even though there was a bathroom full of clean towels…"

"Eh, the bathroom was too far away," Dean said simply. It was true, though. He'd literally stumbled toward the bed and almost passed out when they'd gotten back, he'd been so tired. Sam's bag happened to be within arms' reach and he hadn't wanted to bleed all over the sheets. He looked back down at the boxers. "Sorry 'bout that, though." Sam was right. They really shouldn't be shelling out the money to get new ones.

"It's fine, I guess, but can you help me get the stains out? They dried. Nothing's working."

Dean held up the half-empty bottle of Shout on the table. "This didn't work?"

"No."

"Cold water?"

"Nope."

"Salt water?"

"Uh-uh."

"Peroxide?"

"We're out of peroxide."

"Huh." Dean held up one of the pairs to get a better look at the stain. "Maybe you should try—" But his head whipped up when a female voice interrupted him.

"Hey, Steve?"

It was Mindy/Mandy.

Dean froze, all too aware that he was standing there, in front of the girl he'd just been chatting, next to another dude, scrutinizing a pair of bloody boxers.

A _very_ awkward silence ensued. Mindy/Mandy's eyes got huge as she took in the scene before her, her gaze coming to rest on the boxers.

Dean cleared his throat after a second and not-very-smoothly shoved the boxers behind his back. "Uh…yeah, Mindy?"

"It's Mandy," she said, a little coldly. "I was just gonna ask if you had any dryer sheets I could borrow, but…" Her eyes drifted to Sam.

"Oh," Dean said, a little too loudly. "Uh, yeah. Sure thing."

"No, that's okay," Mandy said, sounding more than a little freaked out. "Obviously and your—" she cleared her throat—"_brother_ are busy right now. I'll go ask somebody else." She turned on her heel and walked away.

_Very _quickly.

"Mandy, wait, we're just—" Dean called after her, but it was no good. "We're just brothers," he added uselessly at her hastily retreating back.

Sam snorted.

Dean wheeled around. "What's so funny?"

"That was." Sam looked like he was barely holding back gales of laughter.

"Dude, that was totally your fault," Dean snarled, throwing the boxers at Sam.

Sam caught them, now laughing in earnest. "How was it my fault?"

"Just…shut up, okay?" He ran an agitated hand through his hair. "Come _on_, why does everyone have think we're gay all the time?"

Sam brandished the boxers. "Well… Can't really blame her, I guess."

"Yeah, whatever."

"Looks like we're gonna get out of here before dinnertime after all, huh?" Sam chuckled.

"Shut up." Without another word, he started transferring Sam's clothes from washer to dryer rather more violently than necessary. A minute or so of silence passed, Dean red in the face and Sam trying and failing to suppress more laughter.

"Got one question for you, though," Sam finally said.

"_What_?"

"Who's Steve?"

_*End*_

**Coming soon…**

_**Winchester Life Lesson Number Two: Don't let your big brother play matchmaker. **_


	2. Chapter 2

_**Things the Winchesters Learned the Hard Way**_

**AN: You probably noticed already, but these first two are a more PG-13 than normal so be warned. But I inflicted girl-related humiliation on Dean in the last chapter, so it's only fair to do the same to Sammy.**

_**Winchester Life Lesson Number Two: Don't let your big brother play matchmaker.**_

"What are you doing here?"

Sam barely glanced up from his laptop screen. He was sitting on his bed, in sweats, the TV on in the background. "What do you mean?" he asked tonelessly.

Evasion. Sam-code for _I don't wanna talk about it. _

"I _mean_, why are you here? Thought you were out, y'know, gettin' some?"

Sam snorted.

"Eh, don't be like that." Dean raised an eyebrow. "You know and I know what was on your mind when you left the bar. The prude act's got nobody fooled, Sammy."

Sam shrugged, face carefully blank.

"Dude, what happened?"

He was silent for a moment. Then, "Not my type."

"Not your _type_?" Dean asked incredulously, locking the motel door behind him and shrugging off his coat, throwing it on a chair. He'd just come back from a late-night fast food run, content to hang out here and maybe catch some pay-per-view while Sam finally, _finally_ got himself laid. Truth be told, Dean had been rather proud of the hand he'd had in the whole thing: he'd blackmailed a Sam who'd been in a rather bad mood after a day of research into talking to the pretty Latino girl at the bar by threatening to introduce Sam to her himself if Sam refused to talk to her. He hadn't exactly thought that, given Sam's track record with women, that Sam would want to sleep with her at all, even if he was interested. But they'd be here for at least the rest of the week on this case, and hey, never say never, right?

He'd been pleasantly surprised when Sam left the bar with her, not even minding that Sam had taken the car and left him to walk because he was so simultaneously proud and amused by the whole thing. She'd needed a ride back to her place, as she'd hitched a ride with her sister and her sister's husband, and the bar was only a few blocks from the motel, so it hadn't been a big deal for Dean to walk back himself. It had been nine-ish when Sam had left with her, and ten when Dean had left the bar himself in search some semi-decent fast food and taken his time walking back to the room.

It was twelve now.

…So obviously something had gone wrong.

"Not your type?" Dean repeated, sitting down opposite Sam on his own bed. "What do you mean she wasn't your type? Man, you sat there with that Anita girl—"

"Allegra," Sam muttered.

"—Allegra, whatever. You sat at the bar for _two hours_ with this Allegra chick talking about _literature_, for cryin' out loud. And I didn't even bother to eavesdrop because it made my freakin' head spin every time I tried. It was disgusting. Of _course_ she was your type."

Sam's jaw clenched. He stared determinedly at the laptop. "Yeah, not so much."

Dean's eyes drifted to an open bottle of vodka sitting close to Sam on the bedside table. "You didn't chicken out, did you?" he asked, teasing.

That got Sam defensive. "No," he said dryly. "I was just going to drive her home. Some of us like to get to know a person a little before trying to get in their pants, you know."

"Oh," Dean said with a suggestive leer. "So how'd that go? How well do you _know_ Allegra now?"

"Pervert."

Dean shrugged. "Your type or not, you _were _gone for a couple hours, dude. Everybody's got urges every once in awhile. So what happened?"

Sam frowned at him. "None of your business."

Dean rolled his eyes. "Oh, come on. You know I'm just gonna keep asking until you tell me."

"Dean," he repeated, annoyed. "Really. I don't want to talk about it."

Of course, Dean completely ignored that, and started guessing anyway, rapid-fire. "Bad breath?" he ventured. "B.O.? Three kids?" He thought for a second. "Tranee in disguise?"

Sam scowled but otherwise ignored him.

"Come on, man. No fair. You gotta give me something."

"No, I don't."

"Toe hair? Communicable disease?" No response. "A husband at home and a Brazilian pool boy on the side?" Still no response. Dean sighed dramatically, but kept firing off the guesses. "Lesbian. Russian assassin. Scientologist." A pause. "She isn't secretly that goblin we're supposed to be after, is she?"

Though he tried to hide it, Sam smiled a little at that one. "No."

"What, then?"

"Just forget it, okay?"

"But—"

"_Please_."

Dean frowned. Sam had actually sounded a little desperate. Okay, maybe he _should _back off…

"Yeah, okay."

Sam nodded once. "Thanks," he muttered.

"Sure." Dean gave it a moment before asking, "That bad, huh?"

"Uh…" He looked anywhere but Dean. "Yeah."

And that got Dean a little worried. Because really, if something bad had happened, like _bad_ bad, it was kinda-sorta-totally his fault for making Sam go talk to the girl in the first place. "Did she…" He leaned forward a bit and scrubbed a hand over his face, wondering how to word this delicately. "Did she, uh, do anything to you?"

Sam looked up. "No."

"Okay…" Dean wasn't sure if he ought to just leave it at that, then. Sam didn't appear to be lying, and _some_ things…well, some things a person certainly had the right to keep to themselves.

…Especially from an adult brother.

…But still.

"Uh…" he began, clearing his throat and trying to push past the incredible awkwardness of the situation. "Are you sure it's something you don't wanna talk about?"

Sam glowered at him. _Yeah, right._

"Nah, really. I mean it. You get a free pass, and—" he picked up the vodka bottle and handed it over to Sam—"and after tonight, we'll never speak of it again."

Sam looked at him skeptically. "Really."

"Yeah."

A beat of silence.

"Promise?"

Dean held up his hands. "Scout's honor."

Sam stared at the vodka bottle in his hand for a long moment, as if scrutinizing the label. Then he huffed a sigh and set the laptop aside, pinching the bridge of his nose.

When he still didn't say anything, Dean asked, tentatively, "She didn't…hurt you or anything, right?" Because if she had, girl or not, Dean would be hard pressed to resist the urge to hunt the skank down and kick her ass.

"No." Sam fidgeted, picking at a hole in his sweatpants. He was still determinedly not looking at Dean. "I already told you, no."

"You sure?"

"Yeah…" Sam rubbed at the back of his neck. Dean noted that his face was going slightly pink.

"Yeah, _but_?" Dean pressed. "I sense a 'but' coming on."

"But," he muttered darkly, unscrewing the cap of the Vodka, "She _would_ have hurt me if I'd given her half a chance." He took a long swig of the vodka. "I'm told that sort of thing has got to be consensual, though," he added, almost inaudibly. His face was now blotchy red, and he'd gone back to fiddling with the hole near his knee.

Dean blinked. "Oh."

_Oh._

He cleared his throat. "So...one of _those_."

"Yep." Sam smiled thinly, obviously mortified. "One of those."

And honestly, Dean didn't know whether to burst out laughing—a dominatrix? And _Sam_?—or feel really, really guilty.

But the guilt thing wasn't so easy to manage when he was having a hard time keeping a straight face.

"'S not funny." Sam mumbled, glaring at him.

Dean shrugged. Maybe making light of the situation would help things. "Eh, it's a little funny."

Sam just kept glaring.

"Nah, but seriously, dude, I don't blame you for bolting. Tried that shit once. Some freaky girl from Fort Lauderdale. Or, uh, St. Augustine. Not sure, actually."

"Really?" Sam smiled, surprised and maybe a little relieved.

"Really," Dean admitted. _Well, there went my dignity for the evening…_ "You were in California at the time, and… Yeah, not really my thing."

"Yeah, me either." Sam shook his head, looking nauseated. "Not sure I get how it could be anyone's thing."

Dean shrugged. "Got me." He thought for a second. "Except maybe the outfits." He sighed appreciatively. "Leather bikini and chains, man. Wasn't a bad look for Miss Fort Lauderdale. Well, uh, 'till she started doing the freaky stuff." He made a face. "Not sure I understood the point of that riding crop."

Sam laughed. "_Riding crop_?"

"Yeah, yeah, laugh it up," Dean grumbled. Geesh, the lengths he went to to be sympathetic towards this kid…

Sam chuckled and handed Dean the vodka. "Sorry."

"No, you're not."

"You're right. I'm not." A pause, and then an embarrassed grin. "Allegra had a dog collar."

Dean gaped. "What? Aw, gross. Really?"

Sam winced. "Yeah. It's…out sitting on the dashboard right now."

"You put it in the car?" Dean asked, appalled. "You actually put that shit in the _car_? You _contaminated_ my baby."

"Sorry. I was kind of in a hurry."

"Alright, well, first thing in the morning we're burning the damn thing." He shook his head. "A friggin' dog collar? Really?"

Sam reached for the bottle. "Really."

Dean shuddered. "Why?"

Sam took another long drink before answering. "Dunno. But she called me...Uh, she called me 'puppy.'" He looked sufficiently wierded out.

"_What_?"

"Yeah."

He met Dean's eyes. A second passed, and then they both burst out laughing.

"_Puppy_?" Dean gasped out, nearly doubled over from cracking up so hard. "You're kidding, right?"

"No." Sam's previous tension seemed to drain away, and he was unable to keep a smile off his face now.

"Wow," Dean chuckled. "That's ten kinds of freaking disturbing."

"I know, right?" Sam flopped back on his pillows and stared at the ceiling. "Man, we have got to finish this hunt so we can get the hell outta this town."

"Agreed." Dean stood back up, intent on grabbing a shower before bed. He looked down at Sam. "Seriously, though. _Puppy_?"

"Apparently."

"Lame. You shoulda asked her for something more awesome, like…I dunno, 'Lone Wolf'."

Sam cringed. "Okay, suddenly I'm not so comfortable discussing this with you anymore."

Dean smirked. "If it'd been me, I'd have been 'Raging Tiger.'"

He had to duck as a half-empty vodka bottle was chucked in the general direction of his head.

***End***

_**Next time, Winchester Life Lesson Number Three: While they might be a good way to get girls, Broadway shows are to be avoided at all costs.**_


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